Dimethylformamide → 1,3,6-Tri(4-methylphenyl)pyrene

HRID 1027319노트

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HRID 1027319 반응식
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[C:4](Br)[CH:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:2]3[CH:15]=[CH:16][C:5]([CH3:6])=[CH:4][CH:3]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[C:4]([C:11]3[CH:10]=[CH:9][C:8]([CH3:7])=[CH:17][CH:12]=3)[CH:3]=2)=[CH:23][CH:22]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 30159691,3,6-Tribromopyrene

생성물 1

HCID 866285911,3,6-Tri(4-methylphenyl)pyrene수율 167.2%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매

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온도
130 °C

실험 절차

Next, a mixed solution of 2.0 g of 1,3,6-tribromopyrene, 2.5 g of 4-methylphenylboronic acid, 5.8 g of tripotassium phosphate, 0.88 g of tetrabutylammonium bromide, 61 mg of palladium acetate and 137 ml of deaerated dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 9 hours. After cooling to room temperature, 800 ml of water was injected, followed by extraction with 200 ml of dichloromethane. The organic layer was washed twice with 100 ml of water, dried over magnesium sulfate and then evaporated. The resultant concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 1.8 g of 1,3,6-tri(4-methylphenyl)pyrene as a pale yellow powder.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with 200 ml of dichloromethane
  3. washThe organic layer was washed twice with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. concentrationThe resultant concentrate
  7. customwas purified by silica gel column chromatography
  8. customvacuum-dried

출처 및 근거

ORD 기록
ord-e068d6f8c028407fb4c7585fa03d15f9
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729530B2

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